Water → 3-{[Phenyl-(3-phenyl propynoyl)-amino]-methyl}-benzoic acid methyl ester

HRID 1623435Notes

Reaction equation

HRID 1623435 reaction equation
[C:1]1([NH:7][C:8](=[O:17])[C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][O:19][C:20](=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27]Br)[CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[CH3:18][O:19][C:20](=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8](=[O:17])[C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 305965N,3-diphenylprop-2-ynamideHCID 517981Methyl 3-(bromomethyl)benzoate

Product 1

HCID 670361553-{[Phenyl-(3-phenyl propynoyl)-amino]-methyl}-benzoic acid methyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Phenyl-propynoic acid phenylamide (951.4 mg, 4.3 mmol), 3-bromomethyl-benzoic acid methyl ester (1.2 g, 5.16 mmol) and Cs2CO3 (2.1 g, 6.45 mmol) were dissolved in DMF (20 ml). The mixture was stirred at room temperature for 16 h. The mixture was poured into water and extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification was by flash column chromatography on silica gel, eluting with hexanes-EtOAc (6:1 and then 4:1) afforded 3-{[phenyl-(3-phenyl-propynoyl)-amino]-methyl}-benzoic acid methyl ester 1.03 g (65%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customPurification
  5. washeluting with hexanes-EtOAc (6:1

Sources & evidence

ORD record
ord-a5588d5168174bca8ad2267fda08428c
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

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